Benzyl Bromide → 5-(Benzyloxy)-2-methylpyridine

HRID 2103973Notes

Reaction equation

HRID 2103973 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Ca+2].[Cl-].[NH4+]>CN(C=O)C>[CH2:9]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 10112Calcium CarbonateHCID 142752-Methyl-5-hydroxypyridineHCID 25517Ammonium Chloride

Product 1

HCID 123972515-(Benzyloxy)-2-methylpyridineYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-2-methylpyridine (2.18 g, 20 mmol) in DMF (15 ml) were added under ice-cooling benzylbromide (4.00 g, 24 mmol) and calcium carbonate (3.30 g, 24 mmol). The reaction mixture was stirred at room temperature for 2 hours. To the reaction mixture was added an aqueous solution of ammonium chloride. The mixture was extracted with diethyl ether, washed with water, dried and concentrated. The obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate) to give 5-benzyloxy-2-methylpyridine (2.04 g).

Workup

  1. extractionThe mixture was extracted with diethyl ether
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-84cbf14389894677a775b22b748450f3
Source dataset
uspto-grants-2009_08
Patent number
US07576198B1

Reaction notes

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